Christian "Webby" Webster has rapped everywhere -- in the school lunch line, at keg parties, on joy rides through Fairfield County. But his skills were truly put to the test the day he landed behind bars.

It was 2009, during his freshman year at Hofstra University on Long Island, N.Y., and Webby had been arrested and held in jail for his participation in an on-campus robbery of a drug dealer. During his week in prison, he challenged other detainees to freestyle rap. It was bold posturing for a kid from suburban Connecticut.

"I knew that if I sucked, I would get my (butt) kicked, no doubt," said Webby, a Norwalk native. "But I did my thing and they said, `You nice, you nice.' I got respect for it. I held my own."

Winning hearts in the rap game isn't easy, especially when you grew up in a suburban condo instead of the projects. But Webby has done just that.

He's opened for the likes of Lupe Fiasco, shared tracks with Connecticut rap giant Apathy and garnered hundreds of thousands of fans (or "ninjas," as he's dubbed them) through his kinetic live performances and heavily-downloaded mix-tapes.

"If you've spent your time perfecting your craft, it doesn't matter where you're from," said Webby, who recently capped off a 24-date, coast-to-coast tour of the United States. "I have a lot of haters, as cliche as that sounds . . . but when I actually rap, they suddenly have a lot less to say."

His brief prison stint notwithstanding, Webby's life scarcely resembles a thug drama. A self-proclaimed "average kid," Webby raps about what he knows: parties, girls, cartoons and of course, his home state ("Connecticut" is tattooed in huge letters across his chest). His music has been described as "frat rap," a hip-hop sub-genre celebrating the debauchery of college life. That being said, he digs much deeper in his rhymes.

"They say this life is gonna chew you up and spit you right back out, but this game's all I know about and I know it ain't fair, but I'm almost there, I know I'm almost there," goes the hook to "Almost There," a song featured on his mixtape, "Best In The Burbs."

"Rapping about parties and girls . . . doesn't prove you're a genius; it just proves you like to have a good time and can put that into a rhyme," Webby said in a recent phone interview. "I also rap about my own life experiences, like having a dream and wanting to go somewhere. That's something everybody can relate to."

Like many emcees coming up in the digital era, Webby has utilized web-based marketing platforms (he's released several mix-tapes via the music website, DatPiff, and dozens of clips on YouTube). But unlike many of the web-inspired fly-by-night success stories, Webby's put in the elbow grease -- he's sold CDs out of his backpack; he's performed at frat and sweet 16 parties; he's constantly practicing his technique.

Webby consummated his love affair with hip-hop in the fifth grade, the same time Eminem, one of his musical heroes, was emerging as a national success. He spent every moment he wasn't in class -- or in detention -- honing his skills.

"He was rapping all the time, nonstop," Josh Lippman, who taught Webby at Greens Farms in Westport and remembers him as "Little Webby." "He has innate verbal gifts."

The son of a teacher (his mother) and a guitarist (his father), Webby was always a solid student. But he had a hard time staying out of trouble. At Greens Farms, he got detention for showing up late to class; at Hofstra, his disciplinary problems became legal ones. The robbery that led to his week in jail also resulted in his expulsion from college. It was then that he got "super serious" about his music career.

"I had always wanted to be a rapper -- that was always my plan A," Webby, who now lives in Fairfield, said. "Since there was no plan B (after college), I decided to make plan A work."

Webby subsequently dropped a series of mix-tapes, including "The White Noise LP," which featured the underground hit single, "La La La," and performed at local venues, including Toad's Place in New Haven and Danbury's Heirloom Arts Theatre. The albums and live shows -- he plays more than 75 a year -- generated considerable buzz, including a mention in XXL Magazine. As more fans have flocked to his camp, so have fellow rappers.

"Chris is an incredible artist," said Apathy, who guests on Webby's latest mix-tape, "Webster's Laboratory." "I see a lot in him that I saw in myself when I was younger. He's so focused. He's not chasing the radio."

Although Webby has received "plenty of offers" from record labels, he has no plans to ink a contract any time soon. His upcoming EP, slated to drop in the fall, will be self-released.

"Right now, we're staying independent," Dana Biondi, Webby's manager, said. "We're keeping the ball in our court; it allows us to do what we want, when we want."

Regardless of what the "haters" think, or whether or not he scores a record deal, Webby can boast of paving his own way. As far as he's concerned, it doesn't matter where you grew up -- all that matters is whether or not you can spit.

"I dare anyone to step in the into my space, and challenge me (to a rap battle)," Webby said. "I will eat their face off, basically."